We all have our unique journey into the world of premium cigars: some of us start later in life, some of us are introduced at a young age (insert minimum legal smoking age for given region), but wherever it is you happen to be on your own personal journey, you’re likely not alone. I’ve found that there are more than a few correlations in these cigar stories, collectively carving out a common set of paths that I like to call “The Evolution of a Cigar Smoker.”

Convenience Store / Machine-made

You are probably around 16 to 18 and you and your buddies are looking for something cool to do. The cigar has a wooden tip and is flavored to an insane level. (Note to the FDA: these are not premium cigars).

Convenience Store Cigars - The Evolution of a Cigar Smoker

Cigar at Celebratory Event

A family member had a baby or got married. You have no clue who made this cigar or how in the world to smoke it. Hopefully someone helped you cut and light it. The smoking experience was likely a disaster and who could blame you, you were so young, so naive.

Fake Cubans on Vacations

You are in Mexico on vacation; the illusive Cuban cigar is finally within reach. You see them on the side of the street, staring at you through their glass-top boxes, begging you to take them home. A small amount of foreign currency later and these gems are all yours!

Poker with Friends or Cigar on Golf Course

You get together with some friends and they hand you a cigar. This is a smaller setting, so you feel comfortable asking how to smoke a cigar or what kind of cigar this even is. You make less of a mess out of smoking and start to see what the excitement is all about.

Flavored Cigar

You get an infused cigar for the first time. Someone told you to check it out. Flavors and intriguing aromas are introduced into the smoking experience and hey, what’s happening? Are you enjoying smoking? Man, this is crazy—maybe you could get into this…

First Lounge Trip

You look up a local cigar shop. You walk in and, lil’ baby bird, you need to learn how to fly. Luckily, the guy at the shop can show you the way and help you get out of the nest. The retailer shows you around, answers some questions, and sets you on your way to a whole new life.

Catalog Fivers – Sampler Packs

You are starting to pick up some steam; you find an ad for cigars online or maybe one of the catalogs finds their way into your hand. Irrelevant. What isn’t is that you order a sampler pack! You are rich in cigars now. A god-king. 10 cigars for 25 bucks! You are a commodities trader of sorts. More cigars than you could ever smoke (at least you assume) arrive at your door. These cigars all suck, but you don’t know it yet. What’s important is that you’re into it!

First Humidor – Desktop 20-count

You need somewhere to store all of these new beauties. You buy a sexy glass-top desktop humidor. It’s a 20-count and you think, “20 cigars? What in the world do I need 20 cigars for?” Are you a mobster or something? You watch a video on how to season your humidor and feel good about the situation.

20-count Cigar Humidor - The Evolution of a Cigar Smoker

Experimentation Phase (AKA Weird “Finding Yourself” Phase)

Through your visits to the shop every once in a while and weeding through your new wealth of dog rockets, you start to develop an opinion. You are beginning to find some stuff you like.

Huge Ring Gauges

What value you have discovered—they sell these cigars the size of a baby for the same price as all the others. All of these sheep in the lounge are smoking these feminine cigars, but no, not you—you are smoking baseball bats like a stud. Some of these behemoths are pretty decent and you could smoke a single stick for like five to six hours, no problem.

Try a Candela – Hate It

What’s this? This cigar looks funny. It’s green, what is it, some sort of lizard cigar?! Ha! Wait, what? It kind of tastes like burnt, decaying hay and not good at all? What the hell? Maybe there is something you are missing…

Eye-opener Cigar

(Now, some of you reading this were lucky enough to have this experience early, like when you skip college in The Game of Life and go directly to work. Some of us weren’t as lucky.)

This cigar is like the red pill from The Matrix. As soon as you smoke it, it’s all over. You belong to the cigars now. This cigar is the one that finally made you understand what was going on within the underlying code. The first great cigar that made everything make sense. For some (many), it’s a Padrón; for me, it was the Perdomo Champagne. This cigar wakes you up to the world of cigars and essentially costs you thousands and thousands of dollars; because, what are you going to do now, stop?

Research Phase

You are now hooked. You are reading everything you can about cigars and their elusive history. You start to learn about companies, factories, and tobacco processing itself. A real passion starts to develop.

Accidentally Putting Cigar in Your Mouth Backwards (Setback)

You are smoking late at night, things happen. Hopefully you didn’t burn yourself. This is definitely a setback.

Smoke Cigar Backwards - The Evolution of a Cigar Smoker

100-count Humidor

Your measly 20-count humidor just won’t cut it anymore and you get a big boy. 100-count. Enough cigars for an army. Okay, a really small army, but still. You are no longer a mere hobbyist, you are a legit cigar authority.

Cigar Bidding

You discover CBid. You become a monster, it takes up most of your time. You are buying cigars you’ve never even heard of and, worse yet, don’t even want! You are installing plugins on your web browser and ignoring personal finance and family members in quest for deals on cigars. You are like a day trader—the Wolf of Wall Street. You are Gordon Gekko—king of cigar-dealing commodities.

Find a Real Cuban

You get your hands on a real cuban cigar. Maybe you bought it, maybe someone gave it to you, it doesn’t matter—you have it! You don’t really get what all the fuss was about…

Join the Dojo

You download the Cigar Dojo app. You log on to check it out and boom, you have done it. You are home. Everyone tells you your humidor is too small.

Ninja Training

Through your newfound membership on the Dojo, you have found your people. You are seeing what everyone is smoking and you can ask questions in a non-threatening environment. You start to buy new and interesting things. You “Never. Smoke. Alone!”


You have realized that your history in humidor purchases has been a charade. You finally start putting your hard-earned dollars to work and upgrade to the cost-effective benefits of a full-on coolidor. You have room to breathe with an actual, realistic cigar storage situation.


You start to venture off the beaten path, at least as far as cigars go. The big companies got you here, but this is your time to try the bespoke. New and interesting blends and varietals are available to you. The stranger the better—up is down, big is bad, craft is king, popular is lowest-common-denominator… If this feels familiar, it’s because you went through this same stage with music in college, and craft beer shortly thereafter.

Trades, Bombs, Swaps

Some of the older or more rare cigars of the past—cigars that you couldn’t simply buy on the open market—are an option for you now. You are trading, bombing, and swapping your heart out.

Hiding Packages from Your Family

You are starting to get packages in at a somewhat-suspicious rate. The delivery guys are your best friends. You are tracking packages all day and, more importantly, trying to get to the packages before your spouse does.

Clever Cigar Storage - The Evolution of a Cigar Smoker

Legit Cuban Phase

You have now gotten into Cubans (or poo-rohs, as you refer to them) in a serious way. Trying different brands (marcas, as you refer to them) and experiencing some of the classics, you have a real understanding of the distinct musky goodness that Cubans bring to the table.

Dojo Releases

You try your first Dojo release—you are (understandably) blown away. How awesome are these Dojo guys? And so handsome too… It’s crazy.

Try a Candela Again – Still Hate It

You decide to try another Candela. You still hate it—what is the deal with these things?

Starting to Appreciate Connecticuts

Where you once thought Connecticuts were grandpa cigars, you have suddenly started to appreciate the subtle, refined intricacies of the shade. Mild is no longer a bad word and these beauties aren’t strictly relegated to morning sessions anymore, occasionally even finding themselves as the headlining act.

Cigar Festivals

You start to travel to mega events. You get to meet retailers and ambassadors you’ve begun to idolize like the rock gods of your youth. The face time with brand owners and companies is the highlight of your year (don’t show it though, dweeb). You get to meet other cigar smokers, maybe some of your friends from the Dojo. Erik Espinosa signed your boob—that was weird.


There is no turning back. You have the itch. You are smoking in zero-degree temperatures, lunch breaks, maybe even a smokin’ wagon. You are full-on obsessed.

Man Cave / HERF Area

You have turned an area in you home into a smoking area. Maybe it’s the garage, maybe it’s a shed, or should you be lucky enough, it’s literally in your house (we have it on file that this has indeed happened—wife approved and everything).

Waiting in Line for Three Hours to Meet Jonathan Drew

A right of passage for any cigar enthusiast.

Cigar Excursion

You visit a factory somewhere. Maybe it’s Nicaragua, Honduras, or the DR. You see the incredible amount of effort it takes to produce a cigar and the number of hands required to bring it from seed to ash—it only makes you more passionate (conversely, this stage may also weed out germ and corona-phobes). You got to blend your own cigar and that was amazing. You probably called the company afterwards and asked them if they’d like to own the rights to produce your blend.

Cigar Excursion - The Evolution of a Cigar Smoker

Start a Facebook Group with the Name “Ash” in It

Congratulations, Ash Me a Question has four members. This is also a right of passage.

Order Supplies and Try to Make Your Own Cigars

Maybe you try your hand at growing tobacco, maybe you order supplies and try to blend or roll your own cigars with the knowledge you gained at the factory. This was all a mistake, you should really leave this to the professionals.


Casual family shopping trips to Walmart suddenly have your humidity senses tingling, as you are strangely drawn to the storage aisle, where tupperware bins and coolers present themselves to you as a mirage of oddly shaped humidors. “Could that be a humidor?” you think to yourself as your children beg for your attention. Maybe you could rig a small fan into that YETI to reduce high-humidity pockets from settling. Maybe your children are detained at the security office—you’ll know in due time, my friend.

Try a Candela and like It?

Someone at a concert gives you a petit candela. The flavors are odd and you can’t stop coughing when you smoke it. It makes the music sound better and the nachos you order from the food stand are legitimately the best thing you have ever eaten. Maybe the pungent green beauty deserves another look or three.

Cigar Nerd (Loser)

At this point your humble cigar hobby has turned into you straight-up being a geek; you can name all the major growing regions, factories, and maybe even a few of the more prominent agricultural operations. You aren’t James Bond smoking like a boss (how you envisioned yourself at the start of this whole journey), you are a dork… But that’s okay, you are one of us now, join the club. Besides, Bond is a little blasé after all, wouldn’t you say?

You get super obsessed with the humidity in your humidor. You are checking every day, you get one that connects to your smartphone and check at work. Wait, don’t tell me you download the data to visualize it through a custom spreadsheet… Come on.

You may also be on a big soft flame kick at this point. Don’t get me wrong, soft flame has a time and a place, just try not to be too pushy about it (i.e. you’ll get over this stage too, so cool your jets… #cigarLighterPuns).

Move to Caribbean – Learn to Roll for Bachelor Parties

You move to Cuba to immerse yourself in the culture. You work at the El Laguito (Cohiba) factory and become a master at entubado bunching. It takes you a decade but you reach Category 9 and are trusted with the deep secrets of Cuban craftsmanship. You finally come home and your family doesn’t recognize you. You roll cigars at bachelor parties.


RH and temperature no longer nag at your ever-waking conscious. These attributes are simply felt. The who’s who of cigar pop culture fades, replaced with engaging conversation and honest friendships. Craft is no longer a buzzword but an expectation, one that is found in large and small cigarmaking operations alike. You feel at one with tobacco, not unlike the spiritual connection of the native Taínos with their sacred leaf, as first witness by Columbus. Hyperbole aside, you live and breath cigars.

Skin Turns into Tobacco

You fall into ooze in a sewer and the first thing you touch is a cigar. You wake up the next day and your skin is veiny and smells of cedar and toasted walnuts. You realize you have become a tobacco man, your skin is literally tobacco. You have to quit your volunteer firefighter gig. This has become a nightmare.

Tobacco Man Monster - The Evolution of a Cigar Smoker

Now, not all of us have taken the same journey. I pray none of you have to know the pain of becoming a tobacco man cigar monster. Sound off in the comments with some of the steps we missed or those that you’ve noticed other smokers falling into along the way.

—Never Smoke Alone!!!

  • Steve Saka Cigars
  • Cigar Wars cigar ratings
Share This
Cigar ratings calculator icon

Download Our Advanced Cigar Ratings Calculator

Join our mailing list to receive Cigar Dojo's Advanced Cigar Ratings Calculator and begin ranking your cigar smoking experiences.

You have successfully subscribed! Please check your email to confirm your subscription. Instructions on how to download the Cigar Dojo Ratings Calculator will then be emailed to you.